[(2R,3S,4S,5R,6R)-6-[[(1S,4R,5R,17R,19S,20R)-8,20-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-19-(hydroxymethyl)-7,9-dimethoxy-3,14-dioxo-2,15,18-trioxatetracyclo[15.2.1.04,13.06,11]icosa-6,8,10,12-tetraen-19-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate

Details

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Internal ID 283c4d21-bd61-462e-ad20-26e81483990d
Taxonomy Lignans, neolignans and related compounds > Lignan glycosides
IUPAC Name [(2R,3S,4S,5R,6R)-6-[[(1S,4R,5R,17R,19S,20R)-8,20-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-19-(hydroxymethyl)-7,9-dimethoxy-3,14-dioxo-2,15,18-trioxatetracyclo[15.2.1.04,13.06,11]icosa-6,8,10,12-tetraen-19-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate
SMILES (Canonical) CC(=O)OCC1C(C(C(C(O1)OC2(C3C(C(O2)COC(=O)C4=CC5=CC(=C(C(=C5C(C4C(=O)O3)C6=CC(=C(C=C6)O)OC)OC)O)OC)O)CO)O)O)O
SMILES (Isomeric) CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@]2([C@@H]3[C@@H]([C@H](O2)COC(=O)C4=CC5=CC(=C(C(=C5[C@H]([C@H]4C(=O)O3)C6=CC(=C(C=C6)O)OC)OC)O)OC)O)CO)O)O)O
InChI InChI=1S/C35H40O19/c1-13(37)49-10-20-25(39)28(42)29(43)34(51-20)54-35(12-36)31-27(41)21(53-35)11-50-32(44)16-7-15-9-19(47-3)26(40)30(48-4)23(15)22(24(16)33(45)52-31)14-5-6-17(38)18(8-14)46-2/h5-9,20-22,24-25,27-29,31,34,36,38-43H,10-12H2,1-4H3/t20-,21-,22-,24+,25-,27-,28+,29-,31+,34-,35+/m1/s1
InChI Key PKBCQPPURBFDJW-LCCFSMFLSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C35H40O19
Molecular Weight 764.70 g/mol
Exact Mass 764.21637904 g/mol
Topological Polar Surface Area (TPSA) 276.00 Ų
XlogP -1.20
Atomic LogP (AlogP) -1.43
H-Bond Acceptor 19
H-Bond Donor 7
Rotatable Bonds 9

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(2R,3S,4S,5R,6R)-6-[[(1S,4R,5R,17R,19S,20R)-8,20-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-19-(hydroxymethyl)-7,9-dimethoxy-3,14-dioxo-2,15,18-trioxatetracyclo[15.2.1.04,13.06,11]icosa-6,8,10,12-tetraen-19-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8050 80.50%
Caco-2 - 0.8813 88.13%
Blood Brain Barrier - 0.6500 65.00%
Human oral bioavailability - 0.6286 62.86%
Subcellular localzation Mitochondria 0.7365 73.65%
OATP2B1 inhibitior - 0.7143 71.43%
OATP1B1 inhibitior + 0.8286 82.86%
OATP1B3 inhibitior + 0.9378 93.78%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.8250 82.50%
BSEP inhibitior + 0.8987 89.87%
P-glycoprotein inhibitior + 0.6799 67.99%
P-glycoprotein substrate + 0.6207 62.07%
CYP3A4 substrate + 0.7105 71.05%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8786 87.86%
CYP3A4 inhibition - 0.8885 88.85%
CYP2C9 inhibition - 0.7832 78.32%
CYP2C19 inhibition - 0.7695 76.95%
CYP2D6 inhibition - 0.9229 92.29%
CYP1A2 inhibition - 0.8417 84.17%
CYP2C8 inhibition + 0.7300 73.00%
CYP inhibitory promiscuity - 0.6977 69.77%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6371 63.71%
Eye corrosion - 0.9869 98.69%
Eye irritation - 0.9160 91.60%
Skin irritation - 0.7813 78.13%
Skin corrosion - 0.9407 94.07%
Ames mutagenesis + 0.5046 50.46%
Human Ether-a-go-go-Related Gene inhibition + 0.7036 70.36%
Micronuclear + 0.5374 53.74%
Hepatotoxicity - 0.7625 76.25%
skin sensitisation - 0.8426 84.26%
Respiratory toxicity + 0.7444 74.44%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.7125 71.25%
Nephrotoxicity - 0.9194 91.94%
Acute Oral Toxicity (c) I 0.3947 39.47%
Estrogen receptor binding + 0.8729 87.29%
Androgen receptor binding + 0.7053 70.53%
Thyroid receptor binding + 0.5455 54.55%
Glucocorticoid receptor binding + 0.7559 75.59%
Aromatase binding + 0.6465 64.65%
PPAR gamma + 0.7665 76.65%
Honey bee toxicity - 0.6833 68.33%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.6400 64.00%
Fish aquatic toxicity + 0.9847 98.47%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 99.95% 85.14%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 99.90% 91.11%
CHEMBL1951 P21397 Monoamine oxidase A 99.09% 91.49%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 99.01% 96.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 94.86% 89.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.51% 95.56%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 93.97% 94.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.08% 86.33%
CHEMBL218 P21554 Cannabinoid CB1 receptor 92.40% 96.61%
CHEMBL2535 P11166 Glucose transporter 91.52% 98.75%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.15% 97.09%
CHEMBL5608 Q16288 NT-3 growth factor receptor 90.93% 95.89%
CHEMBL2581 P07339 Cathepsin D 89.26% 98.95%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 89.23% 92.62%
CHEMBL3401 O75469 Pregnane X receptor 89.13% 94.73%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 88.82% 99.15%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 88.12% 94.45%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 87.70% 96.00%
CHEMBL3060 Q9Y345 Glycine transporter 2 87.35% 99.17%
CHEMBL340 P08684 Cytochrome P450 3A4 85.54% 91.19%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 84.33% 95.89%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 83.53% 89.62%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 83.31% 97.21%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 80.72% 99.23%
CHEMBL4208 P20618 Proteasome component C5 80.42% 90.00%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Trigonotis peduncularis

Cross-Links

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PubChem 162870112
LOTUS LTS0014491
wikiData Q105210285